Sodium Hydroxide → (+-)-N-(cyclopropylmethyl)-1,2,3,4-tetrahydro-8-methoxy-2-naphthalenamine hydrochloride

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To a solution of 2.64 g (15 mmol) 8-methoxy tetralone, 6 g (60 mmol) methylcyclopropylamine HCl and 4.92 g (60 mmol) NaOAc in 30 mL MeOH/THF (1:1) was added HOAc dropwise to adjust the pH to 4-5. The reaction mixture stirred for 15 minutes under N2, then 1.26 g (20 mmol) NaCNBH3 was added. When the reaction was complete by TLC (24 h), 1N NaOH (20 mL) and H2O (200mL) was added to quench the reaction. The solution was extracted with CH2Cl2 (2×500 mL) and the combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The resulting oil was purified by liquid chromatography on 400 g of silica gel 60 (230-400m), eluting with hexane/acetone (3:1). Fractions homogeneous by TLC were combined and concentrated in vacuo to give pure compound as an oil. The HCl salt was formed by using a MeOH/HCl solution. The title compound was recovered by recrystallization as a white solid using EtOAc/MeOH (1.77 g, 44%); m.p. 216°-218° C.

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